cycling_in_tuscany_italy (1)

Biking in Tuscany and Umbria

from  1.050,00

From Assisi to Siena

In this tour you can enjoy the beauty of two beautiful regions such as? Umbria and Tuscany. We wanted to create this particular tour to join together two of the most popular tours offered by us. The tour highlights are: Giotto’s frescoes in Assisi, Spello Roman gates, the city of Cortona, Montepulciano vineyards; “Val d’Orcia” superb landscape, taste the Sagrantino wine, Brunello and Nobile wines, to see the monastery of Monte Oliveto; fomuos the Square del Campo in Siena

  • Holiday Type
    Cycling Holidays
  • Activity Level Moderate
All about the Biking in Tuscany and Umbria.



Assisi and Bevagna – the most famous wine area of Umbria.
Trasimeno Lake: Monte del Lago and San Feliciano fisherman village
Nobile di Montepulciano” wine tasting in a local winery
Pienza and Monticchiello
Buonconvento and the Abbey of Monte Oliveto Maggiore.


We transfer  your luggage

Just leave it at the reception desk with your name tag and you will find it at your next accommodation.

We book  your hotels

We will book double rooms with private bathrooms in 2* or 3* hotels orxb&b or country Inns.

We supply detailed  route notes and maps

At your choice, the route notes can be in English, Italian, French or German and GPS maps

The tour package inclusions and exclusions at a glance
What is included in this tour?Items that are included in the cost of tour price.
  • 7 Nights Accommodation
  • English Speaking Guide with the group
  • Van Escorted
  • All Breakfast and 2 dinners included
  • Luggage transfer
  • Road Book & Maps
  • GPS file available
SHARE YOUR OPINIONItems that are not included in the cost of tour price.

Great route and a really great service, Beppe was absolutely brilliant when he came out to meet us late on a Sunday evening to swap our bike out. Thanks again Beppe!!!

Chris C.

  1. ASSISI Day 1 – Arrival in Assisi

    You will be met at Santa Maria degli Angeli station and transferred to your hotel. Visit this beautiful town which is within 10 minutes walk from your hotel. The next morning you are given your informative kit: road boosk, maps, guide book and vouchers, You will also receive and try your bikes.

  2. SPELLO AND BEVAGNA Day 2 – Assisi – Spello – Bevagna – 50 km

    Today the ride takes you to Spello a very nice and less turistic small town on the Subasio Slopes. You will be riding through olive groves with no major uphill except for the final climb back to Assisi. Night at the same Inn. On the return road you can visit Bevagna going through the most famous wine area of Umbria, the Montefalco Sagrantino DOCG.

  3. CORTE DEL POGGIO Day 3 – Assisi – La Corte del Poggio – 50 km

    On the way to Trasimeno lake an intermediate stop to allows you to visit Deruta a famous ceramic makers’ place and Torgiano, Lungarotti wineries home town; You bike through soft hills and nice villages until you reach la Corte del Poggio in Poggio delle Corti. The road is continuously rolling up and down hill so it is quite a tiring day.

  4. TRASIMENO LAKE Day 4 – Around Trasimeno Lake – Cortona – 50 km

    Discover Montecolognola view poin over the lake, Monte del Lago and San Feliciano fisherman villages; Take a boat to Isola Maggiore where old ladies weave their age old laces and where you can taste a delicious fish at Sauro’s. Then continue to Cortona where you spend the night.

  5. CORTONA Day 5 – Cortona – Montepulciano – 45 km

    Today you enter Tuscany through the wine country of Montepulciano; however, before getting there, a naturalistic tour of the small Chiusi and Montepulciano lakes. Once in Montepulciano, tour this beautiful renaissance town not forgetting a visit to the superb Cantine de Ricci with their vaulted cellars town; have a taste of the “Nobile di Montepulciano ” at Gattavecchi winery, smaller, but very friendly.

  6. MONTEPULCIANO Day 6 – Montepulciano – Buoncovento – 45 km

    After a visit of the San Biagio church, head for Pienza, the beautifull Renaissance town, home to Pope Pius the II and on the way discover the incredible “Crete” landscape with the barren hills, crowned by rows of cypresses. Stop in Montichiello, for a cappuccino (or a glass of wine) with a view.

  7. SIENA Day 7 – Buonconvento – Siena – 50 km

    The road to Monte Oliveto Maggiore Monastery is climbing gently from Buonconvento. Stop and visit the abbey before continuing to Asciano, a small town in the heart of the Crete, and from there to Siena. It is a though day with plenty of ups and downs, but the landscape is superb and very rugged. Spend the night in Siena in a centrally located 3 stars hotel.

  8. YOURS DEPARTURE Day 8 – Visit the town of Siena

    Free time in Siena to visit the town before your departure for your next destination.

Accommodation Level


Day 1 – Assisi

Day 2 – Assisi Loop

Day 3 – Corte del Poggio

Day 4 – Cortona

Day 5 – Montepulciano

Day 6 – Buonconvento

Day 7 – Siena

What happens if I can’t walk / cycle a stage?

If you find the stage too long or if for any reason you cannot walk at all for one day, let us know the previous week and we can arrange for you to go for a short stretch or for the entire stage with the luggage transfer . In some cases a small fee will be asked and you can pay it directly to the driver.

When is the best time of year?

Generally speaking the best season is certainly from April to October; however, it varies with each stage:
– You can only cross the Alps(week 1) from June 15th to September 15th
– The Appennino mountains (week 4) are more pleasurable from mid May to the end of September
– We suggest that you avoid walking among the rice fields (week 2&3) in full summer

How does the baggage transfers work?

Every morning you leave your luggage at the reception of your accommodation, better with a name-tag and you will find it at your arrival at the next accommodation. It has to be delivered by 2pm

Do you provide GPS files for all days?

Yes, on request we can provide GPS files, but we will still supply the paper description just in case your GPS does not work!

Overall Rating


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